19. Round | 26/12/1998 | Southampton FC | - | Chelsea FC | 0:2 | ||||
20. Round | 28/12/1998 | Nottingham Forest | - | Southampton FC | 1:1 | ||||
21. Round | 09/01/1999 | Southampton FC | - | Charlton Athletic | 3:1 | ||||
22. Round | 16/01/1999 | Liverpool FC | - | Southampton FC | 7:1 | ||||
23. Round | 30/01/1999 | Southampton FC | - | Leeds United | 3:0 | ||||
24. Round | 06/02/1999 | Chelsea FC | - | Southampton FC | 1:0 | ||||
26. Round | 20/02/1999 | Southampton FC | - | Newcastle United | 2:1 | ||||
27. Round | 27/02/1999 | Manchester United | - | Southampton FC | 2:1 | ||||
25. Round | 02/03/1999 | Tottenham Hotspur | - | Southampton FC | 3:0 | ||||
28. Round | 06/03/1999 | Southampton FC | - | West Ham United | 1:0 | ||||
29. Round | 14/03/1999 | Middlesbrough FC | - | Southampton FC | 3:0 | ||||
30. Round | 20/03/1999 | Southampton FC | - | Sheffield Wednesday | 1:0 | ||||
31. Round | 03/04/1999 | Southampton FC | - | Arsenal FC | 0:0 | ||||
32. Round | 05/04/1999 | Coventry City | - | Southampton FC | 1:0 | ||||
33. Round | 10/04/1999 | Aston Villa | - | Southampton FC | 3:0 | ||||
34. Round | 17/04/1999 | Southampton FC | - | Blackburn Rovers | 3:3 |